A person whose career has dovetailed with the incentives presented by the confirmation system, a system that punishes creativity and rewards caginess, and who therefore we are forced to construct arguments based on speculation because they have been too careful to let their actual positions leak out.

Brooks locates this type of individual — as is his wont (see for eg. bobos) — in a general sociological group:

About a decade ago, one began to notice a profusion of Organization Kids at elite college campuses. These were bright students who had been formed by the meritocratic system placed in front of them. They had great grades, perfect teacher recommendations, broad extracurricular interests, admirable self-confidence and winning personalities.

If they had any flaw, it was that they often had a professional and strategic attitude toward life. They were not intellectual risk-takers. They regarded professors as bosses to be pleased rather than authorities to be challenged. As one admissions director told me at the time, they were prudential rather than poetic.

Kagan has apparently wanted to be a judge or justice since adolescence (she posed in judicial robes for her high school yearbook). There was a brief period, in her early 20s, when she expressed opinions on legal and political matters. But that seems to have ended pretty quickly…

I knew guys like [John Roberts] in college and at law school; we all knew guys like him. These were the guys who were certain, by age 19, that they couldn’t smoke pot, or date trampy girls, or throw up off the top of the school clock tower because it would impair their confirmation chances. They would have done all these things, but for the possibility of being carved out of the history books for it…

My sense that Roberts has been preparing for next month’s confirmation hearings his whole life was shored up by a glance at the new memos released by the Library of Congress yesterday. As early as 1985, Roberts was fretting about how federal government records disclosed to Congress before confirmation hearings could tank a nomination.

Less important than this minor bit of hypocrisy (which Bill Scher for the Huffington Post mines for all it’s worth) — or perhaps partisan blindness — on the part of David Brooks (and haven’t we all been there?) — is the substance of his critique. Brooks never quite connects the dots — but seems on the verge of making a profound point.

There seems to be a connection between the personality type of Kagan and Roberts — the type of cautious, establishment-minded personality rewarded by our current nomination process — and the tendency of this type of person to defer to the highest authority figure in the American psyche, the President of the United States. In Roberts and Alito, we have 2 of Brooks’s Organization Kids who also happen to be 2 of the most pro-presidentialist Supreme Court justices in history. Though Kagan’s views on this aren’t clear — as she has made some comments indicating an expansive view of executive power only in the context of discussing the views of others — we do know that she felt the Bush administration went too far, unlike Roberts and Alito.

Though I would have preferred a justice more wary of executive power, for me personally, this concern is not enough to give me reason to oppose Kagan’s nomination and appointment. I do want to know more about Kagan’s views on this — to see whether and to what degree she conforms to Glenn Greenwald’s fears (which are, as it should go without saying regarding Greenwald, hyperbolic). Lawrence Lessig has pushed back convincingly against Greenwald on this issue — and of course, Greenwald responded by going ad hominem.

Both Greenwald’s and Brook’s critique ignores the structural element to this pick as neither addresses the degree to which our current confirmation process tends to reward cautious people whose public views are somewhat ambiguous but who are close enough to those in the executive branch that the President nominating them trusts them. The type of person who would meet these criteria would not tend to be the strongest supporters of the Court as a check on executive power. Even aside from the generational category of “Organization Kids,” this would tend to place people deferential to presidential authority into the Supreme Court.

When Obama announced Kagan’s nomination, he praised “her temperament, her openness to a broad array of viewpoints; her habit, to borrow a phrase from Justice Stevens, ‘of understanding before disagreeing’; her fair-mindedness and skill as a consensus-builder.” This sentence echoes countless assessments of Obama himself.

Obama is cool. He makes a show of processing the other side’s viewpoint. He’s more interested in the fruits of consensus than the clarification of conflict. In fact, just as Kagan is praised for giving conservative scholars a hearing at Harvard’s Law School, Obama was praised for giving conservative scholars a hearing on the Harvard Law Review. “The things that frustrate people about Obama will frustrate people about Kagan,” says one prominent Democrat who’s worked with both of them.

Dahlia Lithwick, who I rarely fail to mention, is one of my favorite writers, had a piece a few days ago on what she wants. In a Supreme Court justice that is. And I lightly paraphrase:

Wonky liberal lawyer seeking a hero, a bomb-throwing, passionate, visionary, liberal Scalia for a seat on the Supreme Court!

One of the main facts revealed in all those recent scholarship of the Rehnquist (O’Connor) court, though, was that Scalia’s brash personality and insulting style actually pushed the moderates to the left – or drove them to be less susceptible to being wooed to Scalia’s side in an argument. Though the Court has indisputably moved far to the right since Scalia entered it, seven of the past nine Supreme Court justices have been appointed by Republican presidents. The two appointed by Clinton were moderates chosen to be confirmed by a Republican Congress. Yet, the Court has only moved slowly towards conservative positions. There are many explanations of this, but for anyone who considers the social dynamics of the Court to be significant – and from her article Dahlia seems to be one who does – then Scalia’s antagonistic approach to O’Connor’s sloppy reasoning and Kennedy’s pomposity certainly must be one factor. A brash, bomb-throwing liberal then is exactly what the Court doesn’t need.

What I think it does need is a libertarian-minded liberal who can forge an alliance with Scalia on certain issues – and perhaps Thomas as well. Both Alito and Roberts seem to be enamored of executive power – and perhaps that was why it was they who were chosen. I consider them lost causes. But Scalia and Thomas are conservatives of an older school – one which a contemporary liberal – such as Lawrence Lessig or even Cass Sunstein – has much in common with.

I think Dahlia would be happy with that though – a Lessig, a Sunstein, and a Lawrence Tribe. Perhaps a Harold Koh and an Elena Kagan. Instead of a bomb-thrower, I think Dahlia just wants a liberal with a vision instead of an incrementalist. On that, I agree.

Before the election, some Republicans were trying to gin up some controversy by imputing obscure and extreme judicial views on Barack Obama – focusing especially on remarks he made in July 2007, described here by The Hill:

“[Chief] Justice Roberts said he saw himself just as an umpire,” Obama said. “But the issues that come before the court are not sports; they’re life and death. We need somebody who’s got the empathy to recognize what it’s like to be a young teenage mom.”

Obama said that 95 percent of cases can be judged on intellect, but that the other 5 percent are the most important ones.

“In those 5 percent of cases, you’ve got to look at what is in the justice’s heart, what’s their broader vision of what America should be,” Obama said, adding that justices should understand what it’s like to be gay, poor or black as well.

Nothing less than the very idea of liberty and the rule of law are at stake in this election. We should not let Mr. Obama replace justice with empathy in our nation’s courtrooms.

Putting aside the fact that Calebrisi did not find it necessary to raise his voice against those who used his own legal theory – that of the unitary executive – to actually and explicitly place the president above the law, Calebresi’s concern here is misplaced, as I think you can see just by reading the passage above from The Hill.

But if Calebresi’s half-assed op-ed doesn’t help us understand who Obama would appoint to the Court, then what does?

After all, Supreme Court appointments can be a president’s greatest legacy – affecting policy for many years after a president has gone.

Obama, as a former constitutional law professor, has obviously put a great deal of thought into who he might appoint to the Supreme Court. Many names have been floated – politicians like Jennifer Granholm, Janet Napolitano, Hillary Clinton, and Ken Salazar; academics such as Harold Koh, Elena Kagan, and Cass Sunstein as wel as a number of current judges. With Ruth Bader Ginsburg and John Paul Stevens likely to retire during Obama’s term, and David Souter wishing – according to Jeffrey Toobin, author of The Nine – to withdraw back to the19th century lifestyle he enjoys in New Hampshire away from the Court, Obama could get three – and if Obama is reelected in 2012 – even four nominations to the Court. Justice Scalia will undoubtably do everything possible to avoid retiring during Obama’s presidency, but he is getting older as well – and would be 80 by 2016. Justice Kennedy would be 80 as well – but he does seem to so enjoy being the swing vote that it is hard to see him ever leaving the Court.

Any justices Obama appoints will undoubtably be younger than is traditional – as Bush recently appointed two conservatives in their 50s in Roberts and Alito.

It is also likely that, as the Supreme Court has traditionally been factionalized by race, religion, and gender – from the mid-1800s when there was a “Jewish seat” on the Court and a “Catholic seat” to focus on keeping women and African Americans since the 1980s – Obama will want to appoint at least one woman and on Hispanic to the Court.

The Dynamics of the Court

Obama has spoken of how Justice Warren – as a former politician – was able to win majorities by winning over the other justices. Jeffrey Toobin, writing about the Court over the past decade, has described Sandra Day O’Conner having a similar role during her tenure. In fact, since the Court’s founding, former politicians have had a way of dominating the stately and apolitical Court – beginning with John Marshall. Which is why the first appointment Obama makes should be a former politician – probably a woman. Especially if John Paul Stevens, the unofficial leader of the liberal wing of the Court, retires, Obama will want a strong personality to take his place. As Janet Napolitano is the favorite to become Attorney General, that leaves Jennifer Granholm, Governor of Michigan and a former state attorney general as the most logical choice.

Beyond this first choice of a female politician, Obama’s options are more open.

For his second nomination I would reccomend an academic – Elena Kagan, dean of Harvard Law, or Harold Koh, dean of Yale Law, would be the logical choices here – as both are young and prominent liberals in academia. Koh’s name has apparently been generating real buzz as a potential Obama pick.

Certain to be on any short list is Cass Sunstein is an important legal scholar and a close friend of Obama’s. He recently wrote a book with the conservative economist Richard Thaler about libertarian paternalism.

There is one potential candidate I have not heard mentioned though – and especially if Scalia were to retire from the bench, this former Scalia law clerk, former Reaganite, and former libertarian would be the perfect choice – Lawrence Lessig, whose innovative work founding Creative Commons and now the Change Congress movement, and whose influential work on internet law, copyright and corruption have made him a legal star.

Libertarianism v. Liberalism

With these four appointments, Obama could profoundly alter the Supreme Court’s ideological make-up – by replacing the traditional statist liberals and Rockefeller Republicans on the Court making up it’s current left wing with a charismatic pragmatist, and other liberal, and two libertarian-influenced liberals.